dimethyl(carboxymethyl)sulfonium bromide | 114827-81-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: dimethyl(carboxymethyl)sulfonium bromide
• 英文别名: dimethylthetin bromide；dimethyl(carboxymethylene)sulfonium bromide；(carboxymethyl)dimethylsulfonium bromide；2-pentamethylenesulfoniumylacetic acid bromide；2-Dimethylsulfonioacetate;hydrobromide
• CAS: 114827-81-5
• 化学式: Br*C₄H₉O₂S
• 分子量: 201.084
• InChiKey: VZIWLQJHNSCMDJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.05
• 重原子数：
  8
• 可旋转键数：
  2
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  dimethyl(carboxymethyl)sulfonium bromide 在 磷酸 、 吡啶盐酸盐 、 三氯化磷 作用下， 反应 4.0h， 以447 mg的产率得到1-hydroxy-2-(dimethylsulfonium-1-yl)ethylidene-1,1-bisphosphonic acid
  参考文献：
  名称：

  Activity of Sulfonium Bisphosphonates on Tumor Cell Lines

  摘要：

  We investigated three series of sulfonium bisphosphonates for their activity in inhibiting the growth of three human tumor cell lines. The first series consisted of 6 cyclic sulfonium bisphosphonates, the most active species having an (average) IC50 of 89,mu M. The second consisted of 10 phenylalkyl and phenylalkoxy bisphosphonates, the most active species having an IC50 of 18,mu M. The third series consisted of 17 n-alkyl sulfonium bisphosphonates, the most active species having an IC50 of similar to 240 nM. Three QSAR models showed that the experimental cell growth inhibition results could be well predicted. We also determined the structures of one sulfonium bisphosphonate bound to farnesyl diphosphate synthase, finding that it binds exclusively to the dimethylallyl diphosphate binding site. These results are of interest since they show that sulfonium bisphosphonates can have potent activity against a variety of tumor cell lines, the most active species having IC50 values much lower than conventional nitrogen-containing bisphosphonates.

  DOI：

  10.1021/jm700991k
• 作为产物：
  描述：

  二甲基硫 、 溴乙酸 以 乙腈 为溶剂， 反应 168.0h， 以89.03%的产率得到dimethyl(carboxymethyl)sulfonium bromide
  参考文献：
  名称：

  （羧烷基）二甲基s卤化物的合成，结构和抗菌活性

  摘要：

  一系列ω-卤代羧酸（2-溴代，2-氯代乙酸，3-溴代和3-氯代丙酸）与二甲基硫醚的反应导致形成稳定的（羧基烷基）二甲基s溴化物和氯化物。通过复杂的化学，物理和物理化学方法来确定所获得的盐的组成和结构。所获得的sulf盐对人类和动物的致病菌群具有很高的抗菌和抗真菌活性。

  DOI：

  10.1134/s107036321709002x

文献信息

• Synthesis of 2-Amino-2-deoxy-α-D-altrofuranoside Derivatives from 2,3-<i>O</i>-Isopropylidene-D-glyceraldehyde via Bicyclic β-Lactam Intermediates
  作者：Masao Shiozaki、Noboru Ishida、Sadao Sato

  DOI：10.1246/bcsj.62.3950

  日期：1989.12

  A bicyclic β-lactam (4), obtained from 2,3-O-isopropylidene-D-glyceraldehyde in 3 steps, was converted to methyl 2-benzamido-2-deoxy-5,6-O-isopropylidene-3-O-(3-chlorobenzoyl)-α-D-altrofuranoside (24) through an additional 8 steps by utilizing the β-lactam nitrogen via the oxidative decarboxylation of diacyl peroxide (23). Additionally, it was shown that the bicyclic β-lactam intermediate is a suitable

  由 2,3-O-isopropylidene-D-甘油醛分 3 个步骤获得的双环 β-内酰胺 (4) 被转化为甲基 2-benzamido-2-deoxy-5,6-O-isopropylidene-3-O- (3-氯苯甲酰基)-α-D-呋喃糖苷 (24) 通过额外的 8 个步骤，通过二酰基过氧化物 (23) 的氧化脱羧利用 β-内酰胺氮。此外，研究表明双环 β-内酰胺中间体是 2-amino-3-(branched-chain)-2-deoxy-D-furanoside 衍生物的合适前体。
• Ziegler,E. et al., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1975, vol. 30, p. 755 - 759
  作者：Ziegler,E. et al.

  DOI：——

  日期：——
• Stereospecific synthesis of the lythgoe's ring a aldehyde for the preparation of 1α-hdroxylated tachysterols and calciferols
  作者：Enrico G Baggiolini、Bernard M Hennessy、Jerome A Iacobelli、Milan R Uskokovic

  DOI：10.1016/s0040-4039(00)96052-0

  日期：1987.1
• WO2007/109585
  申请人：——

  公开号：——

  公开（公告）日：——
• Crum Brown; Letts, Jahresbericht ueber die Fortschritte der Chemie und Verwandter Theile Anderer Wissenschaften, 1878, p. 681
  作者：Crum Brown、Letts

  DOI：——

  日期：——